Southeast Asian sources that report regional connection with the Majapahit and Angkor polities reflect upon a rapidly changing fourteenth and fifteenth century world order, the result of new trading opportunities as Europeans were becoming more direct participants in affairs beyond their Western home-lands. In the face of the individualistic and destructive tendencies of the wider global community circa 1500, in the Strait of Melaka region there was less dislocation and isolation than is supposed by many twentieth century scholars. Despite the number of political and religious transitions underway, in the Southeast Asian archipelago and mainland there was a sense of regional self-confidence and progress among societies who had enjoyed over two hundred years of widespread socio-economic success. These successes were the product of the functional international, regional, and local networks of communication, as well as a common heritage that had developed in the Strait of Melaka region during the pre-1500 era. This study not only addresses the role of Majapahit and Angkor in the shaping of regional inclusiveness circa 1500, but also explores the enduring (and often exclusive) legacy of these two early cultural centers among Southeast Asia's twentieth century polities.